Vacation rentals with a pool in Middlesex County

4.87 out of 5 average rating, 86 reviews

An indoor heated saltwater pool is featured in a bright room with natural light streaming through skylights. The pool's clear water reflects playful patterns on the ceiling. Comfortable seating, including a hammock and lounge chairs, is arranged around the pool area.

Home in Aylmer

Indoor pool, hottub & video game room, near beach

Make some memories in our quaint town and stay at our unique family-friendly home with a private indoor heated salt water pool & hottub in the basement. The pool room has a TV, air hockey table, Foosball and basketball game. The fourth bedroom doubles as a board and Video games room/gym and there is a hockey training center on the garage. The fenced backyard has a deck, propane BBQ and seating area, movie screen & projector, trampoline and fire pit (firewood provided). Fun for the whole family!

5 out of 5 average rating, 15 reviews

BlissPoint Sanctuary

Experience a blend of home comfort & hotel luxury. Blisspoint Sanctuary is ideal for all seeking respite & relaxation; travelling professionals, families on vacation. 3 inviting BR incl a King Size master with luxurious ensuite. Full kitchen, theatre-like lounge with recliners & giant screen TV. Secondary lounge boasting a piano, 3-seater recliner & curve TV. Outdoor kitchen provides gas/charcoal BBQ options. Relax in the Heated pool on water hammocks or engage in a fun game of Pool basketball.

A serene outdoor area is depicted, featuring a pool surrounded by lush greenery and vibrant flowers. Tall plants frame the scene, creating a natural separation between the pool and the surrounding yard. The sunlight gently illuminates the space, enhancing the peaceful ambiance.

4.87 out of 5 average rating, 122 reviews

Renovated- Modern-London Home

Enjoy a stylish experience in the beautiful community of Sherwood Forest. Walk to one of the entrances to The Medway Heritage Forest or use the tennis courts or skating rink in the winter. Drive or walk to Western University and University Hospital as well as Sherwood Forest Mall and the Canada Games Aquatic Centre within minutes. Visit the Night life, Restaurants and Specialty Boutique shops on Richmond Row. Near Masonville Mall for great kiosks or Brand Name Restaraunts and Shops. ENJOY!

The exterior of the estate is viewed at night, featuring a well-manicured lawn illuminated by bright outdoor lights. Large windows reflect the warm interior glow, highlighting the spacious design and inviting atmosphere. A seating area is visible on the patio, surrounded by greenery.

4.93 out of 5 average rating, 28 reviews

5BR Luxury Retreat: Hot Tub, Sauna, Pool & More

Welcome to an unparalleled luxury retreat—a 6,800 sq. ft. masterpiece designed for those who appreciate the finest in life. This estate sleeps 16 comfortably, featuring exquisite furnishings, 5 bedrooms, 4 bathrooms, an indoor sauna, oversized hot tub, Olympic pool, heated floors, 2 fireplaces, 2 gourmet kitchens. Located near Boler Mountain, Budweiser Gardens, Storybook Gardens, Museum London 7 min drive to downtown. it’s the ideal destination for an extraordinary luxury getaway in London.

4.97 out of 5 average rating, 94 reviews

A well-maintained pool area features a clean swimming pool surrounded by lounge chairs, inviting relaxation. Two cozy armchairs are positioned nearby, while a shaded structure stands to the left. Lush greenery and a wooden fence provide a natural backdrop, enhancing the tranquil setting.

Guesthouse in Ilderton

Poolside Guesthouse and hot tub

Pool is open for the 2025 season! Welcome to our cozy poolside guesthouse! Whether you want to sit around a fire at night or watch a movie in the air conditioned guesthouse! Enjoy a margarita by the heated pool or a nap on the hammock. Cook your own dinner on the private grill or order in! Relax in the hot tub or catch the game… from the hot tub! You can even watch an outdoor movie under a blanket in front of the outdoor gas fireplace! Plus, the guesthouse opens it door right to the pool!

4.97 out of 5 average rating, 140 reviews

An outdoor area is showcased, featuring a spacious pool with clear waters, surrounded by a concrete patio. Loungers are positioned nearby, alongside a hot tub, while patio furniture offers space for relaxation. Lush greenery adds a natural touch to the private retreat.

Tiny home in London

Newly Built Cabana Home! Pool + Hot Tub!

Enjoy an enchanting stay in this newly built cabana tiny home. Everything is freshly constructed and designed to ensure you relax and unwind. At almost 500 sq feet, the 4 season cabana is a perfect blend of modern and cozy and resides in a premium neighbourhood away from many of the safety concerns that may come with the city's core. The cabana, hottub, pool and backyard will be exclusively yours during your stay which equals privacy for you. Downtown London is a quick 15-20 minute drive.

Top guest favorite

Lush greenery frames the entrance of the home, featuring vibrant ferns and other plants. A welcoming front porch includes a chair with a cushion, providing a cozy spot to enjoy the surroundings. The front door is adorned with a decorative wreath, enhancing the inviting entry.

Home in Port Stanley

5 out of 5 average rating, 15 reviews

SUNNY DAYS at Kokomo beach club/seasonal pool

Welcome to Sunny Days Beach house at Kokomo Beach Club. Only minutes to walk to one of Ontario's most beautiful beaches, stroll along the picturesque streets + stop for lunch at one of the amazing local restaurants. You can relax with the whole family at this peaceful place for your vacation. CLUB HOUSE w GYM & POOL (seasonal opens June 9th 2025) *EV Charger located at clubhouse 🤍fav things; *pickleball courts *walk to the beach *lounging by the pool *the gym *our Comfy King bed

4.77 out of 5 average rating, 105 reviews

A spacious backyard is enhanced by a heated pool, surrounded by a wooden deck and seating areas. The house features a sloped roof and multiple levels, with large windows that invite natural light. A sunset casts a warm glow over the setting.

Home in Dorchester

Pool | Hot Tub | Game Room | Mins to London

Stay 4+ Days and get 10% Off! Perfect for families and groups, the Stardust Retreat offers: ★ Hot tub (Open year round) ★ Seasonal pool (June 1 - Sept 30) ★ Game room ★ Cozy living spaces for comfort and connection ★ Romantic primary suite with soaking tub Nestled near attractions and adventures, we promise an unforgettable stay: ★ 5 min dive to London ★ Pine Knot Golf & Country Club ★ Apple Land Station ★ Mill Pond Ecotrail Gather your tribe and book now for a perfect getaway!

Guest suite in St. Thomas

A landscaped outdoor area features a large, inviting pool with clear blue water. A shaded gazebo is positioned nearby, furnished with seating. Surrounding the pool are lounge chairs, offering a comfortable space for relaxation amidst vibrant greenery.

4.93 out of 5 average rating, 46 reviews

The Glenholm

Built in 1830, "The Glenholm" is one of the oldest homes in the St. Thomas area. This beautiful property is a quick 15-20 minute drive to London and the 401 or Port Stanley. Newly decorated, this space boasts exposed beams in the kitchen, spacious rooms, a quiet setting, a private entrance, beautifully landscaped gardens, and free parking. Whether you need a comfortable place to stay while working in the area or just want to get away to re-charge, we would love to have you.

A well-lit backyard features an inviting in-ground pool, surrounded by landscaped grass and illuminated by string lights. A wooden deck is accessible, along with seating areas, including a hammock. The brick home stands in the background, highlighting a warm nighttime ambiance.

4.86 out of 5 average rating, 65 reviews

Walk-out:Patio:Pool:Private:Open-Concept:

Welcome to our walk-out basement unit nestled in a large and beautiful home in North London! With a private entrance and convenient self-check-in, you'll have easy access to your own serene retreat. The space itself boasts a bright and open layout, providing plenty of room to relax and unwind. Step outside to the covered patio, in ground pool, complete with a dining area and a comfortable hammock, perfect for enjoying meals al fresco or simply lounging in the fresh air.

4.95 out of 5 average rating, 85 reviews

A rustic cabin exterior is featured, enhanced by a spacious deck with outdoor seating. A fire pit is located on gravel in front of the cabin, surrounded by a grassy area and trees. Natural light shines on the wooden facade, highlighting the peaceful rural setting.

Farm stay in Kerwood

Shamrock Clyde Acres

Enjoy a weekend or six days of rest and relaxation in the country. The scenery is beautiful and the cottage accommodations are excellent. Enjoy a private farm experience in a singular secluded cabin. Experience farm living with horses and other animals along a beautiful spring fed creek. Some activities that guests may take part in include, hands on learning about horses, a heated pool, and catch and release fishing.

A modern living room features sleek black leather sofas arranged around a glass coffee table. A wall-mounted television is positioned opposite the seating area, with a minimalist shelf displaying books and decor. Large windows allow natural light to fill the space.

4.97 out of 5 average rating, 29 reviews

8MinVicHospital|4Bed|AirHockey|FullKitchen|Laundry

Welcome to your home away from home! This charming property offers a perfect blend of comfort and convenience, making it an ideal getaway for travellers seeking to explore the vibrant city. With stylish decor and modern amenities, you’ll feel right at home from the moment you step inside. Enjoy spacious living areas, cozy bedrooms, and a fully-equipped kitchen, perfect for unwinding after a day of adventure.

Vacation rentals for every style

Get the amount of space that is right for you

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Apartments

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Popular amenities for Middlesex County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A modern two-story home is showcased, featuring a unique architectural design with a flat roof and large windows. The façade combines gray concrete and warm wooden panels. A paved driveway leads to the dual garage doors, with a neatly maintained lawn and trees visible in the background.

5 out of 5 average rating, 5 reviews

4 Bedroom Peaceful Oasis.

TanyaRating, 5 stars17 months ago

Great place to stay just what we needed

4.29 out of 5 average rating, 7 reviews

A private pool area is highlighted by clear blue water reflecting the sky. Surrounding the pool, a wooden fence offers privacy, while neighboring structures are partially visible. Several loungers line the edge of the pool, providing a comfortable space for relaxation.

Home in Port Stanley

4BR Riverfront Retreat with Private Pool and Yard

CrystalRating, 5 stars10 months ago

exactly as described, kitchen stocked with everything and anything you could need. David was a responsive host. very happy with our stay. will be back again 7 total beds. hot tub was great. toys / floaty in the pool shed for use! river not assisibale from property but a nice view

4.92 out of 5 average rating, 13 reviews

A wooden deck leads to an above ground pool, surrounded by verdant trees and lush greenery. The pool is partially visible, reflecting the sky and providing a serene atmosphere. A set of steps is positioned for easy access into the water.

Home in Port Stanley

The Little Big Cottage, 4 BED, 2 BATH, POOL!

ChrisRating, 5 stars5 months ago

Tyler & Chelsea were extremely communicative & pro-active. They checked-in regularly to make sure we had everything we needed & were enjoying our stay. Fantastic hosts all around! The cottage is cozy, a short walk to downtown, the beach and everything Port Stanley has to offer. Plenty of space for a family and a lovely backyard. 10/10.

A shaded outdoor dining area features a glass-top table surrounded by four chairs. Colorful flowers decorate the wooden fence and nearby planters. The sparkling pool is visible in the background, providing a refreshing setting for meals and gatherings.

MarielRating, 5 stars1 week ago

New place to stay

Mar's Tiki Escape – Pool & Bar

We had an amazing stay at this beautiful property! The place is bright and airy, with plenty of natural light that gives it a welcoming and relaxing vibe. There’s lots of space, with multiple rooms and open areas that are perfect for playing indoor games or just unwinding. One of the highlights was the pool — a great spot to cool off and relax — and the bar area, which added a fun touch for evening hangouts. The digital check-in process was smooth and hassle-free, and the host was incredibly responsive and attentive throughout our stay. Highly recommend this place for groups, families, or anyone looking for a comfortable and enjoyable getaway!

A serene outdoor space features a well-maintained pool surrounded by stone paving, with steps leading to a covered seating area. Lush trees provide a natural backdrop, and comfortable lounge furniture is visible under an umbrella, enhancing the tranquil ambiance.

Home in Grand Bend

4.93 out of 5 average rating, 15 reviews

The Edge of the Woods

BrentRating, 5 stars11 months ago

Overall, a great place to stay with a large family. The pool and hot tub were nice, and there is a beach that is walkable (.75 Miles away). The host was responsive to an issue we had during our stay that was due to a power outage. Our family really enjoyed the house, and the surrounding areas.

A spacious wooden deck surrounds a blue pool, reflecting the sky above. Sun loungers are positioned on one side of the pool, while trees and shaded areas create a serene backdrop. A glimpse of the upper unit and outdoor seating area is visible in the background.

4.67 out of 5 average rating, 48 reviews

BURLINGTON BEACH HOUSE☀️🏝🐚

JeffRating, 5 stars20 months ago

Absolutely BEAUTIFUL STAY!! Highly recommend!!!